Isolation and identification of novel lactones from male Mexican fruit flies

Two isomeric gamma -lactones were isolated from the male Mexican fruit fly, Anastrepha ludens (Loew), Diptera, Tephritidae, and characterized by super(1)H and super(13)C NMR, IR, MS, and X-ray analyses. The structures were (3aR*-(3a direct sum ,4 alpha , 7a beta ))-4-ethenylhexahydro-4,7a-dimethyl-2(3H)-benzofuranone (C sub(12)H sub(18)O sub(2), orthorhombic, P2 sub(1)2 sub(1)2 sub(1), a = 7.448 (6) angstrom, b = 8.582 (4) angstrom, and c = 17.860 (9) angstrom) and (3aR*-(3a direct sum ,4 beta ,7a beta ))-4-ethenylhexadydro-4,7a-dimethyl-2(3H)-benzofuranone (C sub(12)H sub(18)O sub(2), orthorhombic, P2 sub(1)2 sub(1)2 sub(1), a= 6.389 (9) angstrom b = 11.461 (15) angstrom, and c = 15.410 (21) angstrom). X-ray data include final atomic coordinates, bond lengths, bond angles, and molecular numbering schemes. Two alcohols, (Z)-3-nonen-1-ol and (Z,Z)-3,6-nonadien-1-ol, were also isolated from the male Mexican fruit fly. These compounds are currently being evaluated for possible pheromonal activity.